I met Barry Eisler at RT 2009. I was sure I wasn’t going to like him. I mean, here he was at RT, a male author amongst a cavalcade of women, with his long hair and shiny white teeth. But I actually got to sit down and talk with Barry and he’s a pretty interesting person. His background is varied: CIA special operative, former IP lawyer, now writer and most importantly father and husband. Plus, I enjoyed listening to him talk about the process of writing which, to him, involves craft as much as inspiration.

I asked if he would allow me to post a piece about writing and in return I promised to post it near the release date of his newest book,Inside Out: A Novel, a fictional book that at times seems more fact than the newspaper reports. The protagonist in the Rain series is an assassin, an anti hero. How can we cheer for a guy who kills others for a living? The following is Barry’s theory. Got a different one or agree? Leave a comment.

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I have an odd habit of writing protagonists who are killers-‘assassins, black ops soldiers, rogue spies, femme fatales (actually, I guess that would be femmes fatale?). The books are doing reasonably well, so all the killing seems not to be turning people off. This must mean either that the public is exceptionally depraved, or that I'm writing my characters in a way that makes them engaging and sympathetic despite what they do. I don't know that I could offer any useful thoughts on public taste (other than to wonder: did they really need to do a remake of I Spit On Your Grave?), so I'll stick to some thoughts on craft: specifically, how do you make readers care about a protagonist who they should in fact be expected to despise?

I'll focus on my series character John Rain, a half-Japanese, half-American assassin whose specialty is making it look like natural causes, because if you can make a contract killer sympathetic, your only remaining challenge is probably robocallers and people who talk on cell phones in elevators. What's the secret?

First, you have to remember that when we experience a character in a novel, we experience him or her not in isolation, but rather by reference to his or her surroundings. So Rain may be a bad man, but within the corrupt, duplicitous world in which he finds himself, he's actually pretty good. He has a code (no women or children, no acts against non-principals); he has a conscience (he's troubled by some of what he does); he's good to his few friends (Harry and Tatsu). This relativity allows us to like Rain. By the way, I think the best example of this way of making a bad guy into the good guy is Mario Puzo's The Godfather, where the Don comes across as the most admirable character in the book. Sure, he's an organized crime boss and murderer, but within the book's overall setting that's all just a given. What really matters is that the Don is a family man, is straight-laced about sex, won't sell drugs, and is relied on and trusted by his community. In a sense, Puzo turns upside down the ordinary moral universe that we take for granted-‘an amazing case of authorial slight of hand.

Also, at times you get a peek at Rain's past-‘his initial killing experience in Vietnam, for example-‘which makes him much more real to the reader. Real means understandable, and understandable means, possibly, sympathetic. You come to understand not only the events that have shaped Rain; you also are privy to his thoughts and feelings about these events-‘his guilt, his remorse, his regret. Hopefully one comes away from this with a sense that, despite the exterior dissimilarities, Rain is not so different from you or I. After all, he has a conscience, he's troubled by things he's done, he's lonely, he wants to be part of something larger than himself but doesn't know how-‘feelings common to all of us, in which we recognize our common humanity.

In addition to these elements, killers like Rain are appealing because they fulfill (in a safe, fictional environment) certain anti-social wishes that all of us possess. Think about a character like Thomas Harris's Hannibal Lecter, who's so enthralling that by his third appearance, in Hannibal, we're cheering him on! In part, our enthusiasm for Hannibal is a function, again, of the degraded moral universe in which Harris places him (corrupt, incompetent FBI agents; venal, scheming prison administrators; depraved, vicious pursuers); partly, again, it's a function of Hannibal's (admittedly minimal) code of conduct (by his third novelistic appearance he's pretty much only eating the rude or otherwise had-it-coming-to-them). But there's something else going on here, I think: we like Hannibal because we want to be like him. Not that we want to be cannibals, but at some level we do wish we could free ourselves from the rules with which society has surrounded us, we wish we could just do as we please and the hell with the consequences. Wish-fulfillment is part of the allure of evil characters like Hannibal, and there's some of this going on with Rain, too. If you cross Rain, he's doesn't complain about it, he doesn't sue you, he doesn't check into an anger management program. He kills you. Anyone who's ever dealt with irritating coworkers, rude drivers, or any of the thousands of other annoyances of daily life can't help but feel that "damn, that would be kind of nice."

So overall, I think it pays to do two things when you're trying to make an unsympathetic character sympathetic. First, place that character in a universe where, by comparison, he or she looks good. Second, explore the character's inner world. Open up aspects of your character's psyche that readers can relate to. Real villains never think of themselves as villains-‘they think they're the hero, and difficult protagonists think they're the good guy, too. Why do they think that? What's their basis? Explore that, and you'll be heading in the right direction.

I hope that was helpful, and would love to hear from anyone else who's faced similar challenges in making a difficult protagonist sympathetic how you've gone about it. And what works for you, or doesn't work for you, as readers? Any difficult protagonists you've loved despite yourself, or who've turned you off despite the author's efforts? And any thoughts on why? Looking forward to a good discussion-‘thanks.

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Jane Litte is the founder of Dear Author, a lawyer, and a lover of pencil skirts. She self publishes NA and contemporaries (and publishes with Berkley and Montlake) and spends her downtime reading romances and writing about them. Her TBR pile is much larger than the one shown in the picture and not as pretty.
You can reach Jane by email at jane @ dearauthor dot com

I write a female assassin named Gin Blanco. My books are urban fantasy so I think the rules in that genre are a little more flexible about what you can get away with as far as difficult protagonists go, but I do a lot of the same things that you do.

Gin has a code (no kids, no pets, no framing anyone for murder); she’ll do anything for her few friends/family; she lives in a corrupt city/world; she’s haunted by the murder of her family; and she sticks up for the little guy on occasion.

I think the key is making a character tough but still giving them some softer, relatable quirks (Gin loves to cook) and something in their background that explains their choices (her murdered family).

One thing that doesn’t work for me as a reader is the whiny, over-angsty assassin/mercenary/special ops character. Why go to all the trouble of writing a tough character if he/she constantly talks/thinks about how evil they are and what they’re doing is so wrong? That really bugs me since there is a simple, obvious solution for the character — to just quit being an assassin.

I absolutely adore Anne Stuart’s “Ice” series heroes, most of them stone-cold assassins. I had an opportunity to tell her so at a signing once, and when I called them ‘morally ambiguous’ she burst out laughing. “They’re not morally ambiguous, they’re pathological.” She was wearing devil’s horns at the time.

In my upcoming urban fantasy debut, TASTE ME, I’m dealing with the flipside of the difficult protagonist you describe, Barry: the sympathetic – maybe even likeable – villain. He does some horrible things, but through an exploration of his inner life, is not presented as “evil” personified. I look forward to people’s thoughts on this point.

For me, writing about an assassin hero gives me an opportunity to look inside a cold ruthless protagonist and finding something human and lovable. Being a romance writer, I focus a lot on the emotional growth.

I grow up watching a lot of Chinese serial historical martial arts and many of them often featured the lone assassin. Needless to say, I was often very attracted to those characters and find myself looking forward to scenes with them. They very seldom had a happy ending, usually ended alone and without the heroine or dying honorably. In my head, I’d often rewrite these with much more satisfying endings. Anyway, those characters are still my fascination. Parts of my Jed McNeil character reflect this Chinese archetype.

As a reader, they don’t work for me. I can stretch to spies, but I can’t read assasins or mercanaries as sympathetic characters.

I just can’t do moral relativism about murder. Linda Howard had a book ‘Cry No More’ where – several spoilers – a baby is snatched. Even as well as it was written, and as heartbroken as you are for the mother, once she murdered the person who snatched the baby, I lost all sympathy with the character.
Outside of the romance genre that doesn’t matter: you can be interested, or apalled or enthralled by immoral and amoral characters, but inside the genre, they don’t work – for me – because I need to care whether a character gets a HEA. (I read great reviews for Cry No More: I wouldn’t suggest my response was typical.)

While I don’t want the protagonist ‘whiny’ either, if he doesn’t have at least SOME doubt about his actions, it won’t work for me. That internal battle – does the end justify the means? – is what makes this kind of character sympathetic in my eyes.

I also met Barry at RT, and I’d read Fault Line but not his Rain series. Frankly, the idea of thriller featuring an assassin didn’t appeal to me. But after hearing him speak, I was curious enough to get the first 3 Rain books and I was taken in by the writing. Side note: to me, they’re not “thrillers” by my personal definition, but that’s another topic.

I tried to figure out how Barry made Rain into a sympathetic hero. For me, it’s when he shows the emotional, vulnerable side. I actually covered my take on this back on my blog in January, so I won’t go into it here.

I was just talking about this! I think characters like John Rain, Dexter Morgan, Walter White (from Breaking Bad) and even Tony Soprano are likeable because they’re so complicated and multifaceted. We understand why they do the things they do, and even if we don’t agree with their behaviors, we can relate to their dilemmas. Life is not black and white; people are seldom all good or all bad. I love characters that challenge me in this way, make me think and question my own values.

Isn’t part of making the difficult protagonist appealing the fact that his victims aren’t? In part that’s because they’re never as well fleshed out; we don’t see their lives and get invested in them before they become victims, or at least not to the same degree. It reminds me of a deleted scene from the first Austin Powers movie, where the wife of one of Dr. Evil’s minions gets the call about his death at Powers’ hand. It’s funny because it’s such an unusual POV; we never see the bad guys’ underlings as having wives and kids and all that domestic stuff before they get offed. Humor aside, I do wonder if it would be so easy to accept these necessary killings if they went from red shirts to well developed characters. Or maybe I’m still mourning that poor patent examiner in Barry’s Fault Line. Could be that.

As a reader I’m often drawn to military heroes, many of whom have killed in their pasts and continue to kill in the course of the books. Sometimes killing makes them suffer, sometimes their attitude is that they’re just doing their jobs. I think readers generally respond much more positively to this kind of hero than to assassins, mercenaries, or morally ambiguous characters–and yet, military (or ex-military) heroes are still killers, even if they’re killing to protect someone or to right an obvious wrong. And isn’t an assassin also “doing his job?” In the end I think it’s a question of how well the writer redeems the character, whether he’s an all-American Navy SEAL or a cold-blooded contract killer. And it probably goes without saying that the very best of writers are those who can convince us that there’s something to love in even the darkest of villains.

Charlie Huston’s books walk difficult lines with their main characters, and I have really enjoyed a lot of James Ellroy. And George Pelecanos is a master of multifaceted, humane “villains” as heroes of their own stories.

Of course, all of these authors are outside the romance genre. I don’t think these kinds of protagonists have a place currently within the boundries of romance fiction. I think part of the price of having an HEA is the almost tyrannical redemption of any moral ambiguities. Even urban fantasy/paranormal sets rigid boundaries- the “defanged” vampire who only eats animals or murderers, etc.

Sometimes I wish romances went a little bit further, a little bit darker– and not through whiny internal voices. I really liked Judith Ivory’s Black Silk because she made you see the true waste of potential/ humanity when a hero is actually a rake.

For me, I truly enjoy crime fiction, noir, and suspense books when the romance is there and vital to the story. It goes a long way in making those human connections that turn a sociopath into an interesting character. When the romance is poorly written and lame, I detest the books.

There is a huuuugely important, vital romantic sub-plot in Charlie Huston’s Joe Pitt vampire series. And what is James Ellroy’s LA Confidential without the love story?

For me it’s all about the ability to show me why I should care about the character. The best example I can come up with is Swearengen in Deadwood. The first season you mostly hate him, but in the second season, you start to see how much he cares about Trixie and Jewel (my breaking point was when you find out about his going back to rescue Jewel, and you realize that the way he talks to her is almost a form of sibling teasing). The entire series is about anti-heroes (I think Sol Star might be the only truly good guy in the entire series), but once you understand them in context, you find yourself rooting for them and picking favorites (as in when Dan takes on Hearts' henchman; the idea that I'd ever be rooting for Dan was unthinkable until I discover that there's someone worse out there).

John Rain is not a robotic “I-am-an-assassin-with-a-heart-of-gold” character, thanks to Mr. Eisler’s extraordinary storytelling skills. I didn’t like protagonist at first, but the layers were peeled away. You see Rain grow and change. Other authors churn out book after book with formulaic plots and one-note characters. These can be fun reads, but when you are done, that’s it. You don’t give them another thought. They lack the depth of Mr. Eisler’s books, which stay with you long after the last page is read.

First, you have to remember that when we experience a character in a novel, we experience him or her not in isolation, but rather by reference to his or her surroundings. So Rain may be a bad man, but within the corrupt, duplicitous world in which he finds himself, he's actually pretty good.

I think that’s a lot of what made Anne Stuart’s Black Ice, which I reviewed here, work so well for me.

It also helps, IMO, if the difficult protagonist doesn’t justify or rationalize what he does in his own mind too much. That was one of the differences between Black Ice and the subsequent Ice books, which I also enjoyed but not nearly to the same degree. Bastien in Black Ice viewed the organization he worked for as corrupt and had ceased to make excuses for them. Somehow, this made me care about him a lot more.

As an aside, I wonder if there is a different standard for female assassins. There are so many fewer female difficult protagonists than male ones. I think the double standard is still kicking and screaming, at least in the romance genre.

@Hank Shiffman: Have you ever read John Fowles’ The Collector? Brilliant, brilliant book. He makes you kind of understand and feel sorry for a difficult protagonist (budding serial killer) for close to half the book, a section narrated in first person by this man. Then boom, in the second half, he switches to the victim’s POV and her first person narration, and suddenly the protagonist you sympathized with becomes unbearably hateful. The last, short section of the book returns us to his POV, and… well, I won’t give it away, except to say that it’s a totally different experience reading his POV once you have read the victim’s.

Shakespeare also does something a little like this with Edmund in King Lear. No POV switches per se since it’s a play, but we start out understanding Edmund, and end in a very different place after getting to know the victims.

@Janine: I enjoyed Black Ice and Cold as Ice a lot. But I was really disappointed with Isabel’s story (in whatever Ice book it was) because she seemed so strong and capable in the other books, but then, when she got her own book, she didn’t come off as all that capable to me. It was like all the toughness that she’d shown in the previous books just evaporated.

I think people still expect female protagonists to be soft and feminine, instead of as ruthless and cold as their male counterparts are. But whether your hero is male or female, it’s definitely a balancing act to make them tough and still likable at the same time.

Assassin heroes/heroines are not my favorite. I find the professional killer who refuses to accept every job (i.e., the ones who won’t kill honest cops or crusading district attorneys) to be contrived. The characters I find most interesting are those who are conflicted human beings yet who somehow manage to find the heroic inside themselves: Oskar Schindler in real life, the Clive Owen character in “Children of Men” in the movies, or Julian Quayle (might be misremembering the name) in John LeCarre’s “The Constant Gardener” in books. They are the ones who fascinate me, because after a lifetime or ordinariness or petty self-absorption they become brave in the face of frightful adversity and overwhelming odds and I can’t help but wonder how they do it. The Hannibal Lecters or Mafia dons of the literary world don’t interest me nearly as much.

OTOH, I’ve read and liked Howard’s “Cry No More” and some of Anne Stuart’s Ice series, as well as books with characters who killed for a cause but become, nonetheless, quite damaged. It’s a cliche, but it’s all in how the author handles the who and what and why.

Someone above mentioned Shakespeare. I think his Richard the III is one of the most fascinating â€œantiheroâ€s in Literature. Shakespeare's portrayal was a crippled, malevolent, vile human being. And yet, he was fighting for his destiny. He had to â€œclean houseâ€. I saw this performed and as I walked out of the theatre, I was as conflicted as I have ever been. The â€œheroâ€ won, but at such a cost., He knew what the cost would be at the beginning of the play. He accepted it. But how do you accept this awful side of human life? The character of King Richard was portrayed as he was, to move the plot. Did I feel empathy for this awful human? Kind of. It was his destiny, he had to kill to move on.

I agree, Bastion was a great antihero. Ms. Stuart did a great job in building this character, who did what he did, but finally had enough. I read his character as one who gave up the life not to be a better person, but he just couldn't continue the life. The romance of it was almost secondary for me. The choice Bastion made wasn't for the love of a good woman (well not completely anyway). I read him as finally wanting to see daylight again. I did connect with this character, he was a well developed, â€œrealâ€ person.

Great character building/arc is necessary to make the reader believe and feel the frailty of these difficult characters. Showing the reader, rather than telling.

I don’t mind an assassin hero necessarily, although I wouldn’t say it’s my favourite. In the construct of the romance novel fantasy, it can work.

Mr. Eisler had me nodding right up until the bit about Hannibal Lecter. There was never a point in Book 3 that I liked Hannibal that I wished him success, that I wanted to be like him – the book just left a really bad taste in my mouth. Plus, I detested what Harris did to Clarice Starling’s character. She ended up being just as awful at Hannibal IMO.

I did understand what was meant by Not that we want to be cannibals, but at some level we do wish we could free ourselves from the rules with which society has surrounded us, we wish we could just do as we please and the hell with the consequences.
but the analogy doesn’t work for me with Hannibal I’m afraid. Then again, I don’t think much of Dexter either!

(click the link for the back jacket, and ask yourself why big NYC publishers can’t do this well for their books)

I think the notion that people are either non-killers, on the one hand, or have no rules, scruples, or limits, on the other, is mistaken. Human experience (and my own) suggests something more complicated than that. But I could be wrong.

Goes without saying, everything I know, I learned from Shakespeare. :)

Thanks for all the great thoughts, everyone, and sorry I’ve been so scarce — crazy week traveling and getting ready for the INSIDE OUT launch. Jane, thank you again for having me here as a guest… and for not holding my long, flowing tresses against me.

Ah, I think Barry explained it beautifully, with far more eloquence than I could. And given my predilection for Asian men and assassins, it’s no wonder I adore Rain. I just wish he’d get a lot more sex. :>

@Jennifer Estep:
Clearly for many people I failed with Isobel’s book, and yet for me it’s my second favorite after BLACK ICE. I tried to show she was breaking down, no longer able to do what she’d done so brutally for so long, and the return of Killian pretty much brought her to her knees, taking the last of her ruthlessness. That and the child she refused to care about.
But for a number of readers I didn’t manage to set that up properly, which is a shame, because I really adore that book.
However, there are other books waiting to be written. But no, alas, Ice books.

@ Anne Stuart. I haven’t read any of the Ice series but I have Black Ice waiting on my reader. What I have read is Ruthless (and its sequel Reckless) and OMG – Rohan is teh AWESOME!! He’s delicious! I got them from netGalley but I will be buying them too because they were just that good. Looking forward to Breathless too. I suspect I am about to have a backlist glom.

(sorry for going off topic but sometimes one has to take the opportunity to do the fangirl squee!)

[…] protagonist appealing to the reader. Â It sounded similar to Barry Eisler’s post about the difficult protagonist. Â Essentially, you have to make some part of the dark/difficult protagonist heroic, either by self […]

The protagonist in Gift With a Price, the novel I’m working on has trust issues, His mother, pardon me, is an ice bitch, father, a scheming con man financial planner, he is diagnosed with Epilepsy, has numerous failures with docs and drugs, depression, suicide, aggressive tendencies, that is foreign to his nature as he is a sworn pacifist. His character is complex, he’s hetero, but is the unwilling President of the Atherton GSA (Gay,Straight,Alliance). His distrust leads to isolationist tendencies, he wants to be king of his own castle and everyone else should stay the hell away

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